Sodium Bicarbonate → HCID 86591861, compound

Participants

Reaction Conditions

Reaction Steps

step 47a) To a solution of cyclopropylsulfonylamine tert-butyl carbamate (105 g, 4.52 mmol) in THF (9 mL) cooled to −78° C., was added n-BuLi (6.2 mL, 9.2 mmol, 1.6 M in hexane). The mixture was stirred for 1 h at −78° C., and 0.55 mL (0.5 mmol) of fresh 4-(bromomethyl)pyridine was injected in one portion. The fresh 4-(bromomethyl)-pyridine was made from 4-(bromomethyl)pyridine hydrobromide by tributing between aqueous sodium bicarbonate and ether, ether layer was quickly separated, dried (MgSO4), removed solvent in vacuo, and immediately used to the reaction. The reaction mixture was stirred for 5 min at −78° C., changed the bath into ice water, and stirred for another 1 h. The reaction mixture was diluted with pH 4.0 buffer, adjusted pH to 4, and extracted with EtOAc. The combined extractions were dried (MgSO4), concentrated, and purified by pre-HPLC to afford a mixture (only 0.42 g) with 1-(4-pyridyl)-cyclopropanesulfonamide-tert-butylcarbamate and the mixture was used in next step.

Provenance & Evidence